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Triphenylphosphonio‐Substituted 1,2,3,4‐Triazaphospholes and 1,2,4‐Diazaphospholes
Author(s) -
Schrödel HansPeter,
Schmidpeter Alfred
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300114
Subject(s) - chemistry , diazomethane , cycloaddition , dication , ylide , protonation , medicinal chemistry , trimethylsilyl , chloride , derivative (finance) , counterion , nitrogen atom , phosphoryl chloride , photochemistry , organic chemistry , ring (chemistry) , ion , catalysis , financial economics , economics
Several products resulting from the condensation of the bis‐(trimethylsilyl)ylide 1 with PCl 3 serve as synthetic equivalents of a phosphoniophosphaethyne. Cycloaddition reactions with azides lead to phosphonio‐1,2,3,4‐triazaphosphole cations 5, 7 and to the zwitterionic phosphonio‐1,2,3,4‐triazaphospholide 6 . The latter readily undergoes a cycloreversion yielding a phosphoranediyl diazomethane 12 as intermediate. Its cycloaddition affords the diphosphonio‐1,2,4‐diazaphosholide chloride 9a as the final product. 9a is a remarkably stable and unreactive derivative of the two‐coordinate phosphorus. By HCL it is protonated at a nitrogen atom to give dication without any tendency to associate with the chloride counterions.